A client once told me a story that has stayed with me.
Years ago, when she was in her 40s, she and her husband traveled to Egypt to see the Great Pyramids. Many people on her tour had dreamed of making that trip for years. They had saved. They had planned. They had waited.
When the group arrived, they learned what going inside would involve. It would be hot. The passageways were cramped. There were stairs to climb. Getting around would take some effort.
Several of the older travelers realized they couldn’t do it.
They had finally made the trip. They could stand outside and see the pyramids. But after waiting so long, they were no longer physically able to have the experience they had traveled thousands of miles for.
That story illustrates an idea I’ve written about before: We don’t just have a timeline for our bucket list. We have a healthline, too.
But I think the lesson reaches beyond travel.
Some uses of money become less valuable when we postpone them, though not necessarily in financial terms. Their value to our lives can decline because the opportunity to use them well may narrow. This isn’t an argument to spend sooner by default. It’s an argument to count the cost of waiting alongside the cost of acting.
That can make certain financial decisions in midlife more complicated than simply asking, “Can I afford it?”
Waiting is still a decision
Many of us learn that postponing gratification is financially responsible.
Usually, it is.
You save rather than spend everything you earn. You invest for retirement. You build an emergency reserve. You pay down debt. You make sacrifices today so you can have more choices later.
Those habits can serve you well for decades.
The problem comes when postponing becomes the default.
Maybe you want to take a major trip, but you’re worried about the market.
Maybe you’d like to retire, but working another year would make the numbers look even stronger.
Maybe you’d like to reduce your hours, help one of your children, move closer to family, or pay someone to do work you no longer want to do.
Even when the numbers suggest you can afford it, there is almost always a reason to wait.
Maybe next year.
I’d feel better with a little more saved.
Let’s see what happens with the economy.
Once life settles down.
Those aren’t foolish thoughts. But waiting is not necessarily doing nothing.
Sometimes waiting is the decision.
Money has a timing dimension
If you leave money invested instead of spending it today, that money may grow. That’s easy to see on a spreadsheet.
But what else may change during those years?
Your health and energy.
The health of your spouse or parents.
Your children’s availability.
Your willingness or ability to travel.
Your desire to keep working.
The opportunity itself.
After my mother was diagnosed with Stage 4 breast cancer, I decided to take several Fridays off from my job in public accounting. I would spend part of the day doing something for myself, often going for a bike ride, and then spend the rest with my mother.
Those Fridays gave us time together we wouldn’t have had otherwise. It may not have been the best decision for my career or income, but it was the best decision for my mother and me. I’m still grateful I made it.
When thinking about financial decisions in midlife, it’s easy to focus so heavily on preserving money that you overlook what is happening to the rest of your TEAM of Capital: Time, Energy, Attention, and Money.
Money can compound. You can’t recover lost time. Energy and opportunities can narrow.
You could have substantially more money ten years from now and still have less ability to use it in the ways that matter most to you.
What if experiences matter more than inheritance?
I’ve had a version of this conversation in my own family.
I’ve asked at least two of my kids a pretty direct question:
Would you rather we spend more of our money on experiences together, or save more of it so there is more left for you someday?
Their answer: the experiences. Other families might answer differently. What matters is knowing which answer reflects your priorities.
Three of our four kids have finished college. They don’t all have families of their own yet. But they still travel with us.
Travel and other shared experiences have been part of our family life for years. We’ve tried to make spending time together something we value.
I hope that continues when they have families of their own. Maybe the group gets bigger. Maybe the logistics get harder. Maybe the trips change. But I hope the underlying idea remains.
Now imagine the alternative.
Suppose we had skipped many of those experiences so we could leave our children a larger inheritance someday.
Would they necessarily be better off? Maybe financially. But would we, as a family, have created as much value?
That’s a different question.
And it points to something we often miss when considering financial decisions in midlife:
The value of money is not determined only by how much there is. It also depends on when you use it and what it makes possible.
Money spent on a family trip while your children still want to travel with you and can do so may create more value for your family than the same dollars passed to them decades later.
That doesn’t make inheritance unimportant.
It means inheritance isn’t the only way money can benefit the people you love.
The same principle applies beyond travel
Helping your children when help matters most
Suppose you hope to leave money to your children, and they eventually receive it at 60 or 65. What if part of that money could have helped them at 35 or 40 instead?
It might help them buy a home, pay for childcare, return to school, start a business, or get through a difficult transition.
That doesn’t mean you should give away money you may need later.
But once you’ve accounted for your own financial needs, it can be worth asking:
When will this money create the most value?
Sometimes the answer may be after you’re gone.
Sometimes it may be while you’re still here to see what it makes possible.
Changing how much you work
Another year of work can make a retirement projection look stronger. You may save more, delay withdrawals, and give your portfolio another year before you need to draw from it.
But there is another side to the equation. What might you do with that year if you weren’t working? And will a year at 72 necessarily offer the same opportunities as a year at 62?
For some people, one of the hardest financial decisions in midlife is recognizing when earning and accumulating more has become less valuable than reclaiming Time and Energy.
Buying back time
You don’t need a bucket-list dream for this idea to matter.
Maybe you pay someone to clean the house, outsource a task you dislike, spend more for a nonstop flight, move somewhere that makes daily life easier, or get support while caring for an aging parent.
Money spent this way may not produce an asset you can see on a balance sheet.
But it can return Time, Energy, and Attention.
Those are assets, too.
You don’t need perfect certainty
One reason people delay financial decisions in midlife is that they want to be sure.
Sure they won’t run out of money. Sure their plan can withstand a market decline. Sure higher healthcare costs won’t derail it. Sure their children won’t need help.
A good financial plan can’t provide that kind of certainty.
What it can provide is a framework for deciding.
You can model the expense.
Stress-test the plan.
Maintain appropriate reserves.
Ask what you would change if markets struggled.
Identify which decisions are reversible and which aren’t.
That moves you from seeking certainty to developing confidence.
Certainty says:
I know nothing will go wrong.
Confidence says:
I understand the risks, and I have enough margin to adapt if something does.
That is a much more useful standard.
Better questions than “Can I afford it?”
“Can I afford it?” still matters.
But it shouldn’t always be the end of the analysis.
Try adding a few questions:
What would this make possible?
Don’t look only at the cost. What could the decision add to your life or relationships?
What am I protecting by waiting?
More security? More flexibility? A future goal? Name what you’re trying to preserve.
What could I lose by waiting?
Health? Energy? Time with someone? An experience you can’t recreate?
Is this likely to become easier or harder later?
Some opportunities improve with time. Others don’t.
What would need to be true for me to feel comfortable saying yes?
Maybe you want to preserve a certain cash reserve or know that your plan still supports your core goals even if things don’t go as well as expected.
And finally:
If the numbers suggest I can do this, what am I actually waiting for?
Sometimes the answer is financial.
Sometimes it isn’t.
Don’t overlook the risk of waiting
There are at least two kinds of financial regret.
One sounds like this:
I spent money I wish I hadn’t.
The other sounds like this:
I had the money. I could have done it. But I kept waiting, and then the opportunity was gone.
Financial planning gives us clearer tools for measuring the first risk. The second is harder to model, but it deserves attention too.
The travelers at the pyramids had done many things right. They saved. They planned. They waited. They finally made the trip.
But time had changed what the trip could be.
Most of us don’t know exactly where our healthline lies. We don’t know when our parents’ health will change, when the people we love will become less available, or when something we can do easily today will become difficult.
That uncertainty doesn’t always mean we should hurry.
But it shouldn’t always be an argument for waiting either.
Your money exists to support your life.
So if you’ve been postponing something important, a trip, time with family, helping someone you love, reducing your workload, or simply using more of what you’ve accumulated, consider a different question:
Am I waiting because I need to? Or has waiting become my default?
There is wisdom in preparing for tomorrow.
There can also be wisdom in recognizing when tomorrow may make something less valuable than it is today.
Frequently Asked Questions
1. How do I know when I’ve saved enough to spend more?
There isn’t one number that works for everyone. Start by understanding what your future lifestyle is likely to require, the income and assets available to support it, the reserves you want to maintain, and how much flexibility you would still have after making the decision.
The goal isn’t to eliminate every possible risk. It’s to understand whether you have enough margin to adapt if markets, health, taxes, or other circumstances turn out differently than expected.
2. Which financial decisions in midlife are most likely to become harder if I wait?
Pay particular attention to decisions whose value depends on health, energy, relationships, or timing.
Physically demanding travel is an obvious example. Others include reducing work, spending time with aging parents, creating experiences with children or grandchildren, helping family when the help can make a meaningful difference, moving closer to people you care about, or paying for help that gives you back Time, Energy, or Attention.
The common thread is that waiting may leave more money available later while reducing the value of what that money can eventually provide.
3. Isn’t saving more now and spending later the safer choice?
Sometimes it is. But “safer” depends on which risk you’re measuring.
Saving more can reduce the risk of running short financially. Waiting can increase the risk that health, relationships, energy, or circumstances change before you use the money for what matters.
Good planning should consider both risks rather than automatically assuming that postponement is the more responsible choice.
Related Reading
You May Have Enough Money. But Do You Have Enough Life?
Having enough money is only part of the question. The next question is what you want your Time, Energy, Attention, and Money to make possible.
Are You Trying to Decide Whether You Can Stop Waiting?
Sometimes the numbers can help you distinguish between a risk you genuinely can’t afford to take and uncertainty you may simply need to accept.
If you’re facing a decision about retirement, travel, helping family, reducing work, or using more of what you’ve accumulated, schedule a call. We can talk through what the decision could mean for your financial plan and the life you want that plan to support.
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